Here are 50 winter this or that questions, plus 20 winter would you rather questions, grouped into activities, food and drinks, clothes, the holidays, work, and silly scenarios. They work as an icebreaker at work, a classroom warm-up, a family game night, or a poll in your team chat from December through February.
Three favorites to start with: hot chocolate or apple cider?, real tree or artificial tree? and snow day at home or snow day outside?
Jump to a section
- Winter activities this or that (10)
- Winter food and drinks this or that (10)
- Winter clothes this or that (8)
- Holiday this or that questions (9)
- Winter this or that questions for work (7)
- Silly winter this or that questions (6)
- Winter would you rather questions (20)
How to play winter this or that
- In person: read a question and have people move to one side of the room for each answer, or raise a hand.
- On a video call: ask people to type 1 or 2 in the chat, then ask one person from each side to defend their choice.
- In team chat: post one question a day as a poll with two emoji reactions.
- In a classroom: use the activities, clothes and silly sections, which are all kid-friendly.
Winter activities this or that
Snow days, outdoor fun and staying in.
- Build a snowman or make snow angels?
- Snowball fight or build a snow fort?
- Skiing or snowboarding?
- Sledding or snow tubing?
- Ice skating or ice fishing?
- Snow day at home or snow day outside?
- Cabin in the mountains or cozy apartment in the city?
- Hot tub in the snow or fireplace with a book?
- Winter hike or movie marathon?
- Indoor rock climbing or bowling night?
Winter food and drinks this or that
Comfort food debates that can get surprisingly heated.
- Hot chocolate or hot apple cider?
- Marshmallows or whipped cream?
- Gingerbread cookies or peppermint bark?
- Soup or chili?
- Hot chocolate bar or s’mores by the fire?
- Pumpkin spice or peppermint mocha?
- Mac and cheese or grilled cheese and tomato soup?
- Homemade cookies or store-bought cookies?
- Eggnog or mulled cider?
- Pancakes or waffles on a snow day?
Winter clothes this or that
Cozy style choices.
- Fuzzy socks or slippers?
- Knit hat or earmuffs?
- Scarf or turtleneck?
- Gloves or mittens?
- Puffer jacket or long wool coat?
- Snow boots or sneakers no matter what?
- Ugly sweater or matching holiday pajamas?
- Flannel or fleece?
Holiday this or that questions
For holiday parties and the last meeting of the year.
- Real tree or artificial tree?
- Colored lights or white lights?
- Open presents on Christmas Eve or on Christmas morning?
- Wrapping presents or baking cookies?
- Holiday movies or holiday music?
- Secret Santa or White Elephant?
- Give gifts or receive gifts?
- New Year's Eve party or New Year's Eve on the couch?
- Stay up until midnight or asleep by 10?
Winter this or that questions for work
Quick picks for a team meeting, a Slack poll or the office holiday party.
- Holiday party at the office or holiday party out of the office?
- Team potluck or catered lunch?
- Working through the holidays or taking the whole week off?
- Snow day off or snow day working from home?
- Winter team outing or virtual team event?
- Hot drinks in the break room or iced coffee all year?
- Plan next year in December or plan next year in January?
Silly winter this or that questions
Ridiculous choices for a laugh.
- Be a polar bear for a day or be a penguin for a day?
- Wear a swimsuit in the snow or wear a winter coat to the beach?
- Shovel snow all day or walk around in wet socks?
- Live in an igloo or live in a gingerbread house?
- Ride a sleigh to work or ride a snowmobile to work?
- Have a snowman come to life or have a talking reindeer?
Winter would you rather questions
A little longer than this or that, and better for sparking a story.
- Would you rather have snow every day in winter or never see snow again?
- Would you rather spend winter in Hawaii or in a cabin in the Alps?
- Would you rather drink hot chocolate every day or never drink it again?
- Would you rather be too hot or too cold?
- Would you rather go sledding or ice skating?
- Would you rather live where it's winter all year or summer all year?
- Would you rather have a snow day at work or an extra day of vacation?
- Would you rather build the world's biggest snowman or the world's biggest snow fort?
- Would you rather lose your gloves or your hat on the coldest day of the year?
- Would you rather spend New Year's Eve in Times Square or at home with friends?
- Would you rather only eat soup all winter or only eat cookies all winter?
- Would you rather go skiing with a pro or take a winter road trip with friends?
- Would you rather wake up to a foot of snow or a sunny 70-degree day in January?
- Would you rather have a fireplace in every room or a heated floor in every room?
- Would you rather hibernate like a bear or migrate like a bird?
- Would you rather watch the northern lights or see a meteor shower?
- Would you rather give a gift to everyone you know or get one gift you really want?
- Would you rather wear an ugly sweater all day or sing a carol in front of everyone?
- Would you rather plan the holiday party or skip it?
- Would you rather spend a winter day at a spa or at a hands-on workshop making something?
More winter games for your team
Pair these with our 100 Christmas trivia questions, December trivia questions or Christmas movie trivia. Planning a winter team event? KraftStories runs hands-on virtual team building workshops, plus in-person workshops in New York, the San Francisco Bay Area, Honolulu and Austin, and our holiday party alternatives in NYC guide has more ideas.
Frequently asked questions
What are winter this or that questions?
Winter this or that questions give two winter-themed options and ask people to pick one, such as “hot chocolate or apple cider?” or “skiing or snowboarding?”. They're a quick icebreaker for work, school or parties.
What are good winter this or that questions for work?
Good winter this or that questions for work include “holiday party at the office or out of the office?”, “team potluck or catered lunch?”, “snow day off or snow day working from home?” and “plan next year in December or January?”
What are winter would you rather questions?
Winter would you rather questions ask people to choose between two winter scenarios, such as “Would you rather have snow every day in winter or never see snow again?” They take a little longer to answer than this or that questions and often lead to stories.
Are these winter questions good for kids?
Yes. The activities, clothes and silly sections are all kid-friendly and work well as a classroom warm-up or family game.
How do you play this or that on a video call?
Read the question, ask everyone to type 1 or 2 in the chat, then ask one person from each side to explain their pick in one sentence.
